I think you can get to the “damn the man” punk aspect more through certain playbooks, such as the Reporter (which has some strong Transmetropolitan influences) and Pusher.

Also, as you noted, the directives can drive that quite a bit, especially Compassionate.

Jason’s highlights aside, our game hasn’t had a lot of progress so far- we play short sessions, so after three of them we’ve gotten through character creation, basic world-building, and the legwork phase of the mission. It’s probably running a little slow because we are doing more in-character side dialogues (about the wedding the Hacker’s parents are making him go to during the job, for example).